PL135871B1 - Method of obtaining quinoline derivatives - Google Patents
Method of obtaining quinoline derivatives Download PDFInfo
- Publication number
- PL135871B1 PL135871B1 PL1982236836A PL23683682A PL135871B1 PL 135871 B1 PL135871 B1 PL 135871B1 PL 1982236836 A PL1982236836 A PL 1982236836A PL 23683682 A PL23683682 A PL 23683682A PL 135871 B1 PL135871 B1 PL 135871B1
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- Poland
- Prior art keywords
- formula
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- methyl
- compound
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- 238000000034 method Methods 0.000 title claims description 18
- 229940027991 antiseptic and disinfectant quinoline derivative Drugs 0.000 title claims description 4
- 125000002943 quinolinyl group Chemical class N1=C(C=CC2=CC=CC=C12)* 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 28
- 150000003839 salts Chemical class 0.000 claims description 20
- 239000002253 acid Substances 0.000 claims description 18
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 17
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 11
- 229910052739 hydrogen Inorganic materials 0.000 claims description 9
- 239000001257 hydrogen Substances 0.000 claims description 9
- -1 methyl radicals Chemical class 0.000 claims description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims description 7
- 239000011230 binding agent Substances 0.000 claims description 6
- 125000005843 halogen group Chemical group 0.000 claims description 6
- 125000003545 alkoxy group Chemical group 0.000 claims description 5
- QUPDWYMUPZLYJZ-UHFFFAOYSA-N ethyl Chemical compound C[CH2] QUPDWYMUPZLYJZ-UHFFFAOYSA-N 0.000 claims description 5
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical group [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 claims description 4
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical group [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 4
- 239000000460 chlorine Substances 0.000 claims description 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 4
- 239000003814 drug Substances 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 150000002367 halogens Chemical class 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- 150000003248 quinolines Chemical class 0.000 claims description 4
- 229910000104 sodium hydride Inorganic materials 0.000 claims description 4
- 239000012312 sodium hydride Substances 0.000 claims description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 3
- 229910052794 bromium Inorganic materials 0.000 claims description 3
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims description 3
- 125000001424 substituent group Chemical group 0.000 claims description 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 3
- 125000004705 ethylthio group Chemical group C(C)S* 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 150000002431 hydrogen Chemical group 0.000 description 4
- QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 239000003208 petroleum Substances 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric Acid Chemical compound [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Substances OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- HFVMEOPYDLEHBR-UHFFFAOYSA-N (2-fluorophenyl)-phenylmethanol Chemical compound C=1C=CC=C(F)C=1C(O)C1=CC=CC=C1 HFVMEOPYDLEHBR-UHFFFAOYSA-N 0.000 description 1
- ZUGSZYLRCNAKOS-UHFFFAOYSA-N 2-[3-(2-methoxyphenyl)quinolin-2-yl]sulfanyl-n,n-dimethylethanamine Chemical compound COC1=CC=CC=C1C1=CC2=CC=CC=C2N=C1SCCN(C)C ZUGSZYLRCNAKOS-UHFFFAOYSA-N 0.000 description 1
- LFARBJHRSSLIGX-UHFFFAOYSA-N 2-chloro-3-phenylquinoline Chemical compound ClC1=NC2=CC=CC=C2C=C1C1=CC=CC=C1 LFARBJHRSSLIGX-UHFFFAOYSA-N 0.000 description 1
- 150000005642 2-chloroquinolines Chemical class 0.000 description 1
- PXRKCOCTEMYUEG-UHFFFAOYSA-N 5-aminoisoindole-1,3-dione Chemical compound NC1=CC=C2C(=O)NC(=O)C2=C1 PXRKCOCTEMYUEG-UHFFFAOYSA-N 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- SUQPTIULDZJPBI-UHFFFAOYSA-N Cl.Cl.Cl.Cl.Cl.Cl.Cl.Cl.Cl.Cl.Cl.Cl.Cl Chemical compound Cl.Cl.Cl.Cl.Cl.Cl.Cl.Cl.Cl.Cl.Cl.Cl.Cl SUQPTIULDZJPBI-UHFFFAOYSA-N 0.000 description 1
- 208000018522 Gastrointestinal disease Diseases 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 206010020772 Hypertension Diseases 0.000 description 1
- 206010026749 Mania Diseases 0.000 description 1
- 208000019695 Migraine disease Diseases 0.000 description 1
- 208000028017 Psychotic disease Diseases 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 208000024780 Urticaria Diseases 0.000 description 1
- 206010047139 Vasoconstriction Diseases 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 230000003042 antagnostic effect Effects 0.000 description 1
- 239000005557 antagonist Substances 0.000 description 1
- 230000003110 anti-inflammatory effect Effects 0.000 description 1
- 230000001754 anti-pyretic effect Effects 0.000 description 1
- 239000003420 antiserotonin agent Substances 0.000 description 1
- 208000006673 asthma Diseases 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 210000003169 central nervous system Anatomy 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 230000004064 dysfunction Effects 0.000 description 1
- PSLIMVZEAPALCD-UHFFFAOYSA-N ethanol;ethoxyethane Chemical compound CCO.CCOCC PSLIMVZEAPALCD-UHFFFAOYSA-N 0.000 description 1
- 239000002024 ethyl acetate extract Substances 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- NRVFDGZJTPCULU-UHFFFAOYSA-N meda Chemical compound Cl.CN(C)CCS NRVFDGZJTPCULU-UHFFFAOYSA-N 0.000 description 1
- 206010027599 migraine Diseases 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- ARPRLCXPAGXBRL-UHFFFAOYSA-N n,n,2-trimethyl-1-(3-phenylquinolin-2-yl)sulfanylpropan-2-amine Chemical compound CN(C)C(C)(C)CSC1=NC2=CC=CC=C2C=C1C1=CC=CC=C1 ARPRLCXPAGXBRL-UHFFFAOYSA-N 0.000 description 1
- WMSMYWZAPQVNTQ-UHFFFAOYSA-N n,n-diethyl-2-(3-phenylquinolin-2-yl)oxyethanamine Chemical compound CCN(CC)CCOC1=NC2=CC=CC=C2C=C1C1=CC=CC=C1 WMSMYWZAPQVNTQ-UHFFFAOYSA-N 0.000 description 1
- MHZRTNGTWFJGCR-UHFFFAOYSA-N n,n-diethyl-2-(4-methylquinolin-2-yl)sulfanylethanamine Chemical compound C1=CC=CC2=NC(SCCN(CC)CC)=CC(C)=C21 MHZRTNGTWFJGCR-UHFFFAOYSA-N 0.000 description 1
- KBSPNHZTNNSAPF-UHFFFAOYSA-N n,n-dimethyl-1-(3-phenylquinolin-2-yl)sulfanylpropan-2-amine Chemical compound CN(C)C(C)CSC1=NC2=CC=CC=C2C=C1C1=CC=CC=C1 KBSPNHZTNNSAPF-UHFFFAOYSA-N 0.000 description 1
- HYOLQGVNMQNERE-UHFFFAOYSA-N n,n-dimethyl-2-(3-phenylquinolin-2-yl)sulfanylethanamine Chemical compound CN(C)CCSC1=NC2=CC=CC=C2C=C1C1=CC=CC=C1 HYOLQGVNMQNERE-UHFFFAOYSA-N 0.000 description 1
- XMRXKCIELMKQPF-UHFFFAOYSA-N n,n-dimethyl-2-(3-phenylquinolin-2-yl)sulfanylethanamine;hydron;chloride Chemical compound Cl.CN(C)CCSC1=NC2=CC=CC=C2C=C1C1=CC=CC=C1 XMRXKCIELMKQPF-UHFFFAOYSA-N 0.000 description 1
- JRTOLDFHNMOLDW-UHFFFAOYSA-N n,n-dimethyl-2-[3-(4-methylphenyl)quinolin-2-yl]sulfanylethanamine Chemical compound CN(C)CCSC1=NC2=CC=CC=C2C=C1C1=CC=C(C)C=C1 JRTOLDFHNMOLDW-UHFFFAOYSA-N 0.000 description 1
- UMJHMDLXUDUANE-UHFFFAOYSA-N n,n-dimethyl-3-(3-phenylquinolin-4-yl)sulfanylpropan-1-amine Chemical compound C1=NC2=CC=CC=C2C(SCCCN(C)C)=C1C1=CC=CC=C1 UMJHMDLXUDUANE-UHFFFAOYSA-N 0.000 description 1
- 230000002090 nicotinolytic effect Effects 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 210000000192 parasympathetic ganglia Anatomy 0.000 description 1
- 239000004089 psychotropic agent Substances 0.000 description 1
- 208000002815 pulmonary hypertension Diseases 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 201000000980 schizophrenia Diseases 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 208000010110 spontaneous platelet aggregation Diseases 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000001384 succinic acid Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
- 230000025033 vasoconstriction Effects 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D211/40—Oxygen atoms
- C07D211/42—Oxygen atoms attached in position 3 or 5
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/08—Antiepileptics; Anticonvulsants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C233/02—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having nitrogen atoms of carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals
- C07C233/11—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having nitrogen atoms of carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals with carbon atoms of carboxamide groups bound to carbon atoms of an unsaturated carbon skeleton containing six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D215/18—Halogen atoms or nitro radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D215/36—Sulfur atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/22—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D277/28—Radicals substituted by nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
- C07D333/24—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0803—Compounds with Si-C or Si-Si linkages
- C07F7/081—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
- C07F7/0812—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pain & Pain Management (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Quinoline Compounds (AREA)
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB8117642 | 1981-06-09 |
Publications (2)
Publication Number | Publication Date |
---|---|
PL236836A1 PL236836A1 (en) | 1983-09-12 |
PL135871B1 true PL135871B1 (en) | 1985-12-31 |
Family
ID=10522379
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PL1982236836A PL135871B1 (en) | 1981-06-09 | 1982-06-08 | Method of obtaining quinoline derivatives |
Country Status (25)
Country | Link |
---|---|
US (1) | US4435405A (cs) |
EP (1) | EP0066993B1 (cs) |
JP (1) | JPS58965A (cs) |
AR (1) | AR230437A1 (cs) |
AT (1) | ATE11534T1 (cs) |
AU (1) | AU556719B2 (cs) |
CA (1) | CA1189077A (cs) |
CS (1) | CS238624B2 (cs) |
DE (1) | DE3262122D1 (cs) |
DK (1) | DK152428C (cs) |
ES (3) | ES512960A0 (cs) |
FI (1) | FI77451C (cs) |
GR (1) | GR76452B (cs) |
HU (1) | HU186523B (cs) |
IE (1) | IE53064B1 (cs) |
IL (1) | IL65852A (cs) |
IN (1) | IN158970B (cs) |
NO (1) | NO161066C (cs) |
NZ (1) | NZ200878A (cs) |
PH (1) | PH18503A (cs) |
PL (1) | PL135871B1 (cs) |
PT (1) | PT75024B (cs) |
SU (1) | SU1192618A3 (cs) |
YU (2) | YU43269B (cs) |
ZA (1) | ZA823586B (cs) |
Families Citing this family (15)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
ATE27152T1 (de) * | 1982-04-07 | 1987-05-15 | Ici Plc | Chinolin-derivate. |
EP0093521B1 (en) * | 1982-05-04 | 1988-08-24 | Imperial Chemical Industries Plc | Quinoline derivatives |
US4585866A (en) * | 1982-06-09 | 1986-04-29 | Merrell Dow Pharmaceuticals Inc. | Treatment of migraine with substituted tropyl benzoate derivatives |
GB8308601D0 (en) * | 1983-03-29 | 1983-05-05 | Ici Plc | Heterocyclic compounds |
JPS60166406A (ja) * | 1984-02-09 | 1985-08-29 | 株式会社イナックス | 乾式プレス装置の坏土充填方法 |
GB8630071D0 (en) * | 1986-12-17 | 1987-01-28 | Glaxo Group Ltd | Medicaments |
JP2733511B2 (ja) * | 1988-10-22 | 1998-03-30 | 日本臓器製薬株式会社 | 新規アミノアルカン誘導体 |
JPH03147803A (ja) * | 1989-11-06 | 1991-06-24 | Tiger Mach Seisakusho:Kk | 表面多色変化模様のあるコンクリートブロックの製造方法 |
US6566361B2 (en) | 1999-06-30 | 2003-05-20 | Laboratories, Upsa | Azapirone pain treatment |
FR2795645B1 (fr) * | 1999-06-30 | 2001-09-21 | Union Pharma Scient Appl | Nouvelle association pharmaceutique a activite analgesique |
WO2001023350A1 (en) * | 1999-09-28 | 2001-04-05 | Nihon Nohyaku Co., Ltd. | Thioalkylamine derivatives and process for the preparation thereof |
FR2810664B1 (fr) * | 2000-06-27 | 2004-12-24 | Adir | Nouveaux composes cyclopropaniques 1,1 et 1,2-dissubstitues, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
GB0306604D0 (en) * | 2003-03-21 | 2003-04-30 | Curidium Ltd | Second medical use |
ATE511396T1 (de) * | 2007-02-28 | 2011-06-15 | Thromboserin Ltd | Therapeutische zusammensetzungen enthaltend thromboserin oder dessen salze zur verwendung in der prophylaxe oder behandlung von thrombose in patienten mit blutungsrisiko |
WO2009082268A2 (ru) | 2007-12-21 | 2009-07-02 | Alla Chem, Llc | ЛИГАНДЫ α-АДРЕНОЦЕПТОРОВ, ДОПАМИНОВЫХ, ГИСТАМИНОВЫХ, ИМИДАЗОЛИНОВЫХ И СЕРОТОНИНОВЫХ РЕЦЕПТОРОВ И ИХ ПРИМЕНЕНИЕ |
Family Cites Families (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE1049379B (de) | 1959-01-29 | Farbenfabriken Bayer Aktiengesellschaft, Leverkusen-Bayerwerk | Verfahren zur Herstellung von 4 - (tert.-Aminoalkylmercapto)chinolinverbindungen | |
DE430960C (de) | 1924-07-11 | 1926-06-23 | J G Farbenindustrie Akt Ges | Verfahren zur Darstellung von basischen AEthern von Chinolinderivaten |
US1572768A (en) | 1925-06-26 | 1926-02-09 | Winthrop Chem Co Inc | Pharmaceutical product |
US1860286A (en) | 1929-05-16 | 1932-05-24 | Soc Of Chemical Ind | Basic ethers of aryl-quinolines |
GB1511390A (en) * | 1975-12-04 | 1978-05-17 | Pfizer Ltd | Imidazolylalkyl sulphide antifungal agents |
US4343805A (en) | 1978-12-16 | 1982-08-10 | John Wyeth & Brother Limited | Heterocyclic compounds |
-
1982
- 1982-05-19 IN IN381/DEL/82A patent/IN158970B/en unknown
- 1982-05-20 AU AU83863/82A patent/AU556719B2/en not_active Expired
- 1982-05-21 EP EP82302607A patent/EP0066993B1/en not_active Expired
- 1982-05-21 DE DE8282302607T patent/DE3262122D1/de not_active Expired
- 1982-05-21 AT AT82302607T patent/ATE11534T1/de not_active IP Right Cessation
- 1982-05-23 IL IL65852A patent/IL65852A/xx not_active IP Right Cessation
- 1982-05-24 ZA ZA823586A patent/ZA823586B/xx unknown
- 1982-05-25 IE IE1243/82A patent/IE53064B1/en not_active IP Right Cessation
- 1982-05-26 US US06/382,116 patent/US4435405A/en not_active Expired - Lifetime
- 1982-05-27 GR GR68281A patent/GR76452B/el unknown
- 1982-05-28 PH PH27361A patent/PH18503A/en unknown
- 1982-06-02 CA CA000404277A patent/CA1189077A/en not_active Expired
- 1982-06-02 FI FI821965A patent/FI77451C/fi not_active IP Right Cessation
- 1982-06-07 HU HU821828A patent/HU186523B/hu unknown
- 1982-06-08 YU YU1232/82A patent/YU43269B/xx unknown
- 1982-06-08 NO NO821904A patent/NO161066C/no not_active IP Right Cessation
- 1982-06-08 SU SU823450275A patent/SU1192618A3/ru active
- 1982-06-08 PL PL1982236836A patent/PL135871B1/pl unknown
- 1982-06-08 PT PT75024A patent/PT75024B/pt unknown
- 1982-06-08 CS CS824253A patent/CS238624B2/cs unknown
- 1982-06-08 JP JP57097043A patent/JPS58965A/ja active Granted
- 1982-06-08 NZ NZ200878A patent/NZ200878A/en unknown
- 1982-06-09 ES ES512960A patent/ES512960A0/es active Granted
- 1982-06-09 DK DK257782A patent/DK152428C/da not_active IP Right Cessation
-
1983
- 1983-01-14 ES ES519006A patent/ES519006A0/es active Granted
- 1983-08-30 AR AR294046A patent/AR230437A1/es active
- 1983-09-01 ES ES525298A patent/ES8502688A1/es not_active Expired
-
1984
- 1984-11-08 YU YU1882/84A patent/YU42905B/xx unknown
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